Fleishman is in Trouble review: An upside-down look at gender, marriage, and the New York skyline

Jesse Eisenberg stars in this well-crafted comedy drama

Fleishman is in TroubleJesse Eisenberg as Toby Fleishman.  (Matthias Clamer/FX)
Fleishman is in Trouble - Jesse Eisenberg as Toby Fleishman. (Matthias Clamer/FX)

The long-awaited adaptation of Taffy Brodesser-Akner’s 2019 novel Fleishman is in Trouble is streaming on Disney+ from 22 February.

In the pilot episode of this eight-part miniseries, viewers leap into the bare bedroom of 41-year-old divorcee Toby Fleishman (Jesse Eisenberg). Curled up in foetal position, Toby is awoken by buzzing notifications from his newly downloaded dating apps.

A slew of ‘self-actualised’ women await response to seductive pictures and suggestive messages. His friend Libby’s voice (Lizzy Caplan), also a character in her own right, impeccably narrates the circumstances of Toby’s life.

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It’s a specific reality we come to understand: Toby, having recently emerged from a nasty divorce with nasty ex-wife Rachel, is now more wanted than ever.

Watch a trailer for Fleishman is in Trouble

As a 41-year-old Jewish doctor on the Upper East Side, his sexual prospects are limitless. He now spends days in other people’s livers and nights under other people’s sheets. Introduced to the “emancipation” of women (or lack thereof) by the twenty-somethings he sleeps with, Toby still can’t bring himself to choke one: “I took an oath, that could kill someone.”

At the forefront of his world are Rachel (Claire Danes), his newly-reacquainted-with friends Libby Epstein and Seth Morris (Adam Brody), and his two children, Hannah (Meara Mahoney Gross) and Solly (Maxim Swinton).

The show’s upside-down skyline opening set (also the novel’s cover), is a clever clue into the story we are about to be told. Toby’s life is turned upside down when Rachel unexpectedly drops the kids off at his apartment and doesn’t return for days.

Meara Mahoney Gross as Hannah, Jesse Eisenberg as Toby Fleishman, and Maxim Swinton as Solly in Fleishman is in Trouble. (Linda Kallerus/FX)

Juggling work, children, and run-ins with her snooty friends, Toby looks back on his life and questions why he married Rachel in the first place. The absolute confusion of Toby’s life is effectively inhabited by Eisenberg’s permanent facial expression.

As he races through the streets, sweaty, exhausted, and hungry for answers, he demonstrates something refreshing: the urgency of a well-crafted plot and complexity of a well-written protagonist.

Contrasted with the sharp edges of the New York City skyline is the show’s rounded cinematography. Close-up visuals of turning staircases and revolving doors of women are effective in making viewers feel like they’re entering Toby’s life via snow globe.

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Cut between scenes of sharp dialogue — “She’s a drunk. Alcoholic? Person with alcoholism?” — are spinning montages of Jesse Eisenberg in about every sex position you can imagine. He complements his Mark Zuckerberg-like straightforwardness with the sex drive of a 1990’s sitcom’s womaniser.

Directed by Little Miss Sunshine’s power couple Jonathan Dayton and Valerie Faris (Ruby Sparks/Living with Yourself), Fleishman’s pilot episode meets the mark by engaging in unique conversations around age and gender.

Jesse Eisenberg as Toby Fleishman & Lizzy Caplan as Libby Epstein. (Linda Kallerus/FX)

As the friends discuss Toby’s shiny, new prospects, Libby divulges doubts about her own tortured marriage: “It makes a girl start to wonder how she might do on the produce market.”

At age 41, it becomes clear that divorced men are reaching their peaks while divorced women are reaching their breaking points. Like author and showrunner Brodesser-Akner herself, narrator Libby is a former journalist at a men’s magazine comparable to GQ.

Understanding the differences between her circumstances and those of a man’s seems to be her modus operandi and the two women’s telling of Toby Fleishman’s story is an effective turning over of the typical male gaze.

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Narrator and friend, Libby acts first as an unbiased reporter of the friends’ lives. Later in the season, her wry, generous, and authentic narration will grant Rachel narrative license, turning Toby’s on its head. The show’s multiperspectivity is not lost on Solly, who, at the end of the pilot, makes an acute observation regarding his science project on relativity: “The same thing happens at the same time,” he says. “But if someone else observes it at a different angle, it can also be true.”

Claire Danes as Rachel Fleishman and Jesse Eisenberg as Toby Fleishman. (Linda Kallerus/FX)

Thus, while a seemingly regular story — another rich white male as a protagonist? —Fleishman is in Trouble is instead a typical man’s story uniquely told by a woman.

With a rich cast full of worthy comeback stars, living in Fleishman’s world feels oddly and peacefully like watching real life happen.

Straightforward yet complex, emotional yet deadpan, particularly male yet powerfully female, the show offers an entertaining story with a powerful under layer enjoyable for a diverse range of viewers.

The entire Fleishman is in Trouble series premieres on 22 February on Disney+.